3,4-diphenyl-Δ²-1,2,4-triazolin-5-one | 2039-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,4-diphenyl-Δ²-1,2,4-triazolin-5-one
• 英文别名: 3,4-diphenyl-1,2,4-triazolin-5-one；4,5-diphenyl-2,4-dihydro-3H-1,2,4-triazol-3-one；4,5-diphenyl-2H-1,2,4-triazol-3(4H)-one；4,5-diphenyl-2,4-dihydro-[1,2,4]triazol-3-one；2,4-dihydro-4,5-diphenyl-3H-1,2,4-triazol-3-one；4,5-Diphenyl-2,4-dihydro-[1,2,4]triazol-3-on；3,4-diphenyl-1H-1,2,4-triazol-5-one
• CAS: 2039-00-1
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: FRQZGESFDFFMNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-diphenyl-Δ²-1,2,4-triazolin-5-one 在 copper(l) chloride 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.08h， 生成 4,5-diphenyl-2-[4-(perhydroazepino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 4,5-diaryl-2-[4-(t-amino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones

  摘要：

  A series of 4,5-diaryl-2-[4-(t-amino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones were synthesized and characterized by infrared spectrum (IR), H-1-NMR spectra and elemental analyses. Investigation of their antimicrobial activity was performed. Antimicrobial activity profile of the title compounds were evaluated against Gram- positive bacteria, Gram-negative bacteria and fungi. The synthesized compounds displayed different degrees of antimicrobial activities as shown in Table 3. Compound 12 was the most active one. This may be attributed to 4,5-diphenylsubstituent on the triazoline-3-one ring and the nature of the amino groups at terminal acetylenic moiety.

  DOI：

  10.1007/s00044-011-9840-9
• 作为产物：
  描述：

  苯甲醛吖嗪 在 氢氧化钾 、 乙醇 、 三氯化铁 作用下， 生成 3,4-diphenyl-Δ²-1,2,4-triazolin-5-one
  参考文献：
  名称：

  Bailey; McPherson, Journal of the American Chemical Society, 1917, vol. 39, p. 1334

  摘要：

  DOI：

文献信息

• [EN] MTP INHIBITING ARYL PIPERIDINES OR PIPERAZINES SUBSTITUTED WITH 5-MEMBERED HETEROCYCLES<br/>[FR] PIPERIDINES D'ARYLE OU PIPERAZINES SUBSTITUEES PAR DES HETEROCYCLES A 5 RAMIFICATIONS INHIBANT LA MTP
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005085226A1

  公开（公告）日：2005-09-15

  The present invention is concerned with novel aryl piperidine or piperazine compounds substituted with certain 5-membered heterocycles having apoB secretion/MTP inhibiting activity and concomitant lipid lowering activity. The invention further relates to methods for preparing such compounds, pharmaceutical compositions comprising said compounds as well as the use of said compounds as a medicine for the treatment of hyperlipidemia, obesity and type II diabetes (Formula (I)). The invention further relates to methods for preparing such compounds, pharmaceutical compositions comprising said compounds as well as the use of said compounds as a medicine for the treatment of atherosclerosis, pancreatitis, obesity, hyper­triglyceridemia, hypercholesterolemia, hyperlipidemia, diabetes and type II diabetes.

  本发明涉及新颖的芳基哌啶或哌嗪化合物，其被某些含有apoB分泌/MTP抑制活性和伴随的降脂活性的5-成员杂环取代。该发明还涉及制备这种化合物的方法，包括所述化合物的药物组合物以及将所述化合物用作治疗高脂血症、肥胖症和2型糖尿病的药物的用途（公式（I））。该发明还涉及制备这种化合物的方法，包括所述化合物的药物组合物以及将所述化合物用作治疗动脉粥样硬化、胰腺炎、肥胖症、高甘油三酯血症、高胆固醇血症、高脂血症、糖尿病和2型糖尿病的药物的用途。
• Nonprostanoid prostacyclin mimetics. 3. Structural variations of the diphenyl heterocycle moiety
  作者：Nicholas A. Meanwell、Michael J. Rosenfeld、Ashok K. Trehan、Jeffrey L. Romine、J. J. Kim Wright、Catherine L. Brassard、John O. Buchanan、Marianne E. Federici、J. Stuart Fleming、Marianne Gamberdella、George B. Zavoico、Steven M. Seiler

  DOI：10.1021/jm00097a007

  日期：1992.9

  4,5-Diphenyl-2-oxazolenonanoic acid (2) and 2-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetic acid (3) were previously identified as nonprostanoid prostacyclin (PGI2) mimetics that inhibit ADP-induced aggregation of human platelets in vitro. The effects on biological activity of substitution and structural modification of the 4- and 5-phenyl rings of 3 was examined. Potency showed a marked sensitivity

  4,5-二苯基-2-恶唑壬酸（2）和2- [3- [2-（4,5-二苯基-2-恶唑基）乙基]苯氧基]乙酸（3）先前被确定为非前列腺素前列环素（PGI2 ）在体外抑制ADP诱导的人类血小板聚集的模拟物。考察了3的4-和5-苯基环对取代和结构修饰的生物活性的影响。效能显示出对将取代基引入这些芳族环的显着敏感性，并且只有双-4-甲基衍生物9j（IC50 = 0.34 microM）与母体结构3（IC50 = 1.2 microM）相比具有增强的效能。在苯环的邻位或间位取代，被噻吩基或环己基部分取代，或限制在平面菲系统中产生的化合物不是ADP诱导的血小板聚集的有效抑制剂。相比之下，杂环部分的变化表明，SAR的严格性要低得多，并且发现许多5和6元杂环可有效替代2和3的恶唑环。二苯甲基部分可作为4,5-的有效等排体自13aad以来的二苯环杂环化合物显示出与3相似的血小板抑制活性。除了3,4,5-三苯基吡唑衍生物13g以外，与类似取代的3
• Synthesis of 1,2,4-Triazol-3-imines via Selective Stepwise Cycloaddition of Nitrile Imines with Organo-cyanamides
  作者：Pallavi Sharma、Shreesha V. Bhat、M. R. Ranga Prabhath、Andrew Molino、Elisa Nauha、David J. D. Wilson、John E. Moses

  DOI：10.1021/acs.orglett.8b01673

  日期：2018.7.20

  A convenient method for the synthesis of 1,2,4-triazol-3-imines through a selective, formal, 1,3-dipolar cycloaddition of organo-cyanamide ions with nitrile imine dipoles is reported. Hydrolysis of the 1,2,4-triazol-3-imines yields the corresponding 1,2,4-triazol-5-ones. A stepwise mechanism, supported by DFT calculations, is invoked to explain the reaction selectivity.

  报道了一种通过有机腈酰胺离子与腈亚胺偶极的选择性，形式，1,3-偶极环加成反应合成1,2,4-三唑-3-亚胺的简便方法。1,2,4-三唑-3-亚胺的水解产生相应的1,2,4-三唑-5-酮。调用DFT计算支持的逐步机制来解释反应的选择性。
• Ramachander; Srinivasan, Current Science, 1959, vol. 28, p. 368
  作者：Ramachander、Srinivasan

  DOI：——

  日期：——
• Surendra Nath,T.G.; Srinivasan,V.R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15, p. 603 - 606
  作者：Surendra Nath,T.G.、Srinivasan,V.R.

  DOI：——

  日期：——